Issues with penetration?

I'm 20 years old and a virgin, currently in a long distance relationship with the love of my life. He's visiting soon and I really want to have sex with him, I feel mentally ready. But in past experience I've had issues with penetration. I couldn't even us tampons up until recently, and when my boyfriend has fingered me in the past it's hard to get more than one finger in. I'm confused as to what's going on, because I feel aroused and comfortable around him. Help??